Understanding the mechanism of Pd-catalyzed allylic substitution of the cyclic difluorinated carbonates.
We present a mechanistic investigation of Pd-catalyzed allylic substitution of cyclic gem-difluorinated carbonates 1 and 4, previously employed in the synthesis of 3',3'-difluoro-2'-hydroxymethyl-4',5'-unsaturated carbocyclic nucleosides in 17 steps. The substitution features a reversal of regioselectivity caused by fluorine.
Xu
Jun
J
Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032, China. xujun@mail.sioc.ac.cn
Qiu
Xiao-Long
XL
Qing
Feng-Ling
FL